Coloring composition



Patented Dec. 16, 1941 COLORING COMPOSITION Alphonse T. Flore, Passaic,N. J., assignor to Burton T. Bush, Inc., New York, N. Y., a corporationof New Jersey No Drawing. Application August 24, 1940, Serial No.354,109

13 Claims.

This invention relates to lip-coloring and lipstaining compositions, andmore particularly to such compositions which contain halogenatedfluoresceins.

The object of this invention is to provide improved compositions of thetype which actually stain the lips and which do not impart coloringthereto merely by reason of a layer of coloring material deposited onthe lips.

Another object of this invention is to furnish compositions in which thechief stain-causing ingredient is substantially all in its most activeform, i. e., dispersed in solution.

A further object is to obtain compositions of the lip-staining orindelible type before noted, in which the amount of irritation which maybe caused by such compositions to the user thereof is reduced to aminimum.

A still further object is to provide lip-coloring compositions of theindelible type which attain a rapid development of color after beingapplied to the lips.

Other objects of this invention will be apparent to those skilled in theart from the following description.

Lip-coloring compositions, e. g., lipsticks, as is known, ordinarilycontain several ingredients. Animal and vegetable oils, waxes, modifierssuch as lanolin. dyes, lakes and perfumes, etc., are commonly-usedlipstick raw materials.

The practice employed in the lipstick art may be outlined as follows:

The ingredients comprising the wax base are usually melted together andstirred to assist solution. The dye is separately dispersed in castoroil and enough of thewax base is added thereto so as to form a softpaste at room temperature. The paste is then ground through a roller orointment mill. The balance of the wax base ingredients is then added,the entire contents being reheated and stirred until the wax base hasbeen dispersed. Perfume and/or other special purpose ingredients may beadded just prior to pouring the contents into suitable molds. Thetemperature of pouring is ordinarily about above the solidifying pointof the lipstick. The contents must be stirred continuously up to thepoint of pouring. After cooling below the solidification point, thelipstick may be removed from the molds.

In,lipstickmanufacture, castor oil has found general use because of itspeculiar properties. It is used as a dispersant for dye. It is a thick,viscous oil and among the most suitable of the vegetable and animal oilsin lipsticks. It is considered to be a good solvent for halogenatediluoresceins; it is also miscible with animal and vegetable oils as wellas true-ester-type waxes.

In spite of its very general use in lipsticks manufacture, castor oilhas certain disadvantages. It is only slightly miscible with mineral oiland other hydrocarbons, thereby precluding the use of all but relativelysmall amounts of such materials. Moreover, there is a definite tendencyfor lipsticks containing castor oil and halogenated fluorescein tobecome rancid. Further, the solvent powder of castor oil for halogenatedfluorescei'ns is actually quite low, viz: about of 1%. The disadvantagesof this low solvent power in connection with lipsticks will be shownhereinafter.

I have discovered that lipstick of improved properties can be obtainedby replacing part of the castor oil with tetra hydro furiuryl alcohol.The compatibility of the castor oil-tetra hydro furfuryl alcohol withmineral oils and other hydrocarbons is quite satisfactory.

A further discovery of this invention is the practicability ofcompletely eliminating the castor oil as an ingredient in lipsticks bythe use of tetra hydro iurfuryl alcohol and certain secondary solvents.Examples of such solvents are lauryl lactate, ethylene glycol monoricinoleate, propylene glycol mono laurate, glyceryl mono ricinoleate,cyclonol and ethyl tartrate and ethyl citrate.

A very important advantage obtained by the use of tetra'hydro furfurylalcohol is its superior solvent power for the halogenated fluorescindyes. Whereas /g "of 1 part of tetra bromo fluorescein in 100 partscastor oil is the limit of solubility therein, in tetra hydro furfuiylalcohol at least 28 parts of the dye will dissolve in 100 parts of thealcohol. The increased solvency of the dye in tetra hydro furfurylalcohol results in lipsticks of increased color intensity when appliedto the skin. This is probably so because the dye is in solution and thislatter state is the most eflicient for the dye. When castor oil alone isused only /z% of the dye, as before indicated, is in solution. Theundissolved dye (e. g. if the dye were present to the extent of 4% ofthe weight of castor oil, 3 of the dye would be undissolved) is not asefiective in its staining power as it would be were it dissolved.

The increased color-imparting eiliciency of lipsticks containing tetrahydro furfuryl alcohol renders it possible to reduce materially anyirritation which may be associated with lipsticks 65 containing thehalogenated fluoresceins'. This is brought about by the need of muchless dye than heretofore required. Another contributing factor to thematerial reduction in irritation when tetra hydro furfuryl alcohol isused, is the fact that the dye, being dissolved therein, is in a formconducive to less irritability than were it in the undissolved or solidform.

It is also noteworthy to mention that the rapidity of stain developmentof the lips is greater in lipsticks containing tetra hydro furfurylalcohol. A possible explanation of this fact, although one to which I donot wish to bind myself, is that the dye is substantially all dissolved;consequently it is in its most active state.

The process of making lipsticks has been improved by this inventionalso. A solution of the dye in tetra hydro furfuryl alcohol may bestored indefinitely without necessitating any agitation thereof beforeuse. Heretofore, it has been necessary to either use freshlyprepared dyedispersions or to agitate same before use in lipsticks. Moreover, thepresent invention permits of the simple heating together of theingredients without continual agitation thereof during the lipstickmaking.

It is believed that this invention was not foreseeable. The high solventpower of tetra hydro furfuryl alcohol for halogenated fluoresceins wasunexpected. This can be more readily realized by reference to thefollowin data, obtained by measuring the amount of the tetra bromofluorescein which dissolves in 100 parts of the material tested, theparts here as in this entire patent specification, being by weight.

6 percent not soluble.

1 percent completely soluble. 2 percent not soluble.

28 percent completely soluble. percent soluble.

1 percent not soluble.

Propylene glycol mono ester of capric ac 'Ietrs hydro iur'luryl alcoholCastor oil The lip-coloring compositions embraced by this invention arethose containing one or more halogenated fiuoresceins. These arereaction products of halogenated phthalic acid and resorcinol; they aresometimes referred to as di-hydroxy halogenated fiuoranes. Examples ofsuch materials within the scope of this invention are4,5-di-bromo-3,6-fluorane diol; 2,4,5}?tetrabromo-12,13,14,15-tetra-chloro-3,6, fluorane diol;4,5-di-chloro-3,6-fluorane diol; 2,4,5}? tetrabromo-3,6 fluorane diol(tetra bromo fluorescein) When desired, of course, lakes or toners maybe employed to obtain the shade sought.

Although lipsticks have been used in this speciflcation for the purposeof illustrating the invention, it is to be understood that they are onlya preferred embodiment thereof. The invention is capable of beingemployed in other lip-coloring or staining compositions, e. g. liquids,pastes or rouges intended for coloring or staining the lips. The termslip-coloring and lip-staining on the one hand, and coloring and stainingon the other are used interchangeably herein except where otherwiseclearly indicated. Although the application of this invention tolipstlcks has been particularly shown herein, it will be understood thatsuch is merely by way of illustration and not by way of limitation.

The permissive and preferred amounts of the various ingredients used mayvary over relative ly wide limits. Based on the lipstick composition,the amount of halogenated fiuorescein may vary from /2 to 5% althoughamounts from may be used in amounts from 5 to 25%.

to 2% are ordinarily used. The amount of castor oil may vary from 15 to50%. Where secondary solvents are used, the amounts thereof are of thesame order. Tetra hydro furfuryl alcohol The preferred amounts of theforegoing are 0.5-2% for the halogenated fluorescein, 15 to 35% forcastor oil or so-called secondary solvents, and 5 to 20% for the tetrahydro furfuryl alcohol. Examples illustrating the practice of theinvention follow:

The first five ingredients may be called the wax base part. These aremelted together and stirred to assist solution. The tetra bromofluorescein is dispersed in the castor oil and a sumcient amount of thewax base added to render the mass a soft paste at room temperature. Thismass is then passed through either a roller or ointment mill. To themilled mass the balance of the ingredients is added, and the entirebatch reheated and stirred until the wax base has been dispersed. Thebatch is poured into suitable molds at a temperature of C. and aftercooling in the molds, the lipsticks are removed therefrom. Stirring iscontinued up to the point of pouring.

Present process:

Beeswax 15 Ozokerite 5 Spermaceti 5 Lanolin l0 Vaseline l5 Dye solution50 *Dye solution contains 75 parts eastor oil, 25 parts tetra hydrofurfuryl alcohol, 4 parts tetra bromo fluorescem. All the ingredientsare heated under agitation to a temperature sufficient to melt the wax,e. g. C. After a clear solution is obtained, the contents are cooled toabout 65 C. and then poured into suitable molds, which are chilled. Theresulting lipsticks are removed in the usual manner. No stirring isnecessary after a clear solution has been obtained.

It is understood that the invention is not limited by the foregoing butis to be construed as broadly as permissible in view of the prior art,limited solely by the appended claims.

What is claimed as new is:

l. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and a halogenated fluorescein.

2. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and a bromo fluorescein.

3. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and a chloro fluorescein.

4. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and tetra bromo fluorescein.

5. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and 4,5-di-bromo- 3,6-fluorandiol.

6. A lip-coloring composition containing tetra hydro furfuryl alcohol,waxes, and 4,5-di-chloro- 3,6-fluorandiol.

7. Lipstick containing tetra hydro furfuryl alcohol and a halogenatedfluorescein.

13. The process of making lipsticks which comprises heating ahalogenated fluorescein with ingredients normally employed in lipsticksin the presence of tetrahydro furfuryl alcohol, and at a temperaturesufficiently high to attain a liquid condition and maintaining saidtemperature until a clear solution is obtained, pouring the contentsinto suitable molds, and cooling to form lipsticks.

ALPHONSE T. FIORE.

